


The Tushy Technique

by GavinIsaNuisance



Category: Original Work
Genre: Anal, Anal Fingering, Anal Sex, Anal Training, Bi-Curiosity, Bisexual Female Character, Cheating, Clothed Sex, Cowgirl, Doggy Style, F/F, F/M, Infidelity, Interracial Relationship, Lesbian, Lesbian Anal, Lesbian Anal Sex, Lesbian Sex, Missionary Position, Spanking, Strap-Ons, Threesome - F/F/M, Yuri, blowjob, f/f - Freeform
Language: English
Status: In-Progress
Published: 2020-06-17
Updated: 2020-06-23
Packaged: 2021-03-04 05:48:53
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 13,436
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24778669
Author URL: https://archiveofourown.org/users/GavinIsaNuisance/pseuds/GavinIsaNuisance
Summary: A prudish young Cora is taken aback when her boyfriend Jeff insists they spice up their sex life with anal sex. A disgusted Cora is consoled by her lesbian roommate Maddie who enjoys anal intercourse with females. A "joke" is hatched where Maddie suggests she train Cora's asshole for Jeff and Cora then hatches the idea to carry out this wickedly sexy plan. What predictably happens is Cora finds herself in a bisexual love triangle between her boyfriend and her quirky lesbian roommate.
Relationships: Cora/Jeff, Cora/Maddie, Cora/Maddie/Jeff
Comments: 3
Kudos: 10





	1. Five Stages of Anal Grief

**Author's Note:**

> This work is entirely fictitious, any relationship to persons living or dead is completely coincidental and entirely unintentional. All persons depicted in a naked and/or sexual nature are 18 and up.

Los Angeles, California. The once prominent tinsel-town is a shell of its former self. A place of palm trees, decadent manors, and movie stars is now a hotbed of homelessness, negligently high taxes, and glistening in a thick layer of smog from the high rises of Downtown, to the syringe-lined shores of Venice Beach.

Still, it is a place where many Americans and non-Americans come to stake their claim and gain a piece of that fleeting California dream. Which takes us to the story, because nobody likes three pages of exposition. We're in the Westside, it's the part of LA you think about when talking about LA: The Hollywood Sign, Santa Monica, Beverly hills, Bel Air and the like. In the Hollywood neighborhood, which is not at all as glamorous as portrayed in the movies sits a trashy apartment complex along Franklin Avenue near Highland. In apartment eight of this dilapidated dump lived two women, who are our focus in this backdoor debauchery.

The first was Cora Gutierrez. Now, despite her very Hispanic name you would stereotypically think she was an LA native, there you would be wrong. Cora grew up in the sleepy Podunk, and not to mention freezing cold town of Fargo, North Dakota. A city famous for the Cohen Brothers' movie of the same name where all of one scene was actually set there. Cora was one of a handful of Hispanic families growing up in her sleepy one-horse town and she always had aspirations of leaving, as anyone with sanity would. She went to school at the University of California Los Angeles to get a degree in Public Relations, where she excelled and found the one thing every Angeleno dreams of; something more valuable than gold itself: a steady career with good benefits and room to grow. She had a strange upbringing, her mother Bonita was the only Hispanic Jew she'd ever meet while her father Jorge was a traditional Catholic. These two religious views always confused her and she tried not to talk about it much. But, she was always happy, and bubbly; always wanting to see the best in people. As she appeared, she was thick in the right places. She had a cute face with long brown hair, caramel skin, perky C-cup breasts, nice legs, a tight pussy and an ass that wouldn't quit. Cora had a very thick butt, something she was personally proud of because it always started a party in every boy's pants. She was truly a sight to behold.

Her roommate, found on Craigslist was Madison Crittenden, who went by Maddie. Maddie was Caucasian and was an LA native—well, sort of. Maddie grew up a bit south in Orange County, you know, where the real housewives are from. She was from the more bustling suburban town of Newport Beach, I think that's where The O.C. was set. She came from two parents who lived exceptional lives. Her father Brett was a lawyer and aspiring politician while her mother Lila was an extremely successful if not tenacious real estate agent, and both did quite well for themselves. Maddie was also a UCLA alumnus but for their film school, and was an aspiring actress. One more pertinent bit of news about Maddie is that she was a lesbian. Her parents, products of the ultra-conservative Newport Beach society were actually more disappointed by Maddie's acting aspirations than her sexual orientation, but she had placated them by getting a few speaking gigs on sitcoms and was recently acquired by the prestigious William Morris agency.

But as LA rents are criminally insane, she was always tight on cash, and for that matter, so was Cora. Maddie also didn't fit the mold of your garden variety lesbian. She was deeply religious, something that always calmed her parents' fears of her falling into a life of sin. She was Catholic but volunteered at the local Methodist church on Highland and Franklin because she could always use more Jesus in her life but also several celebrities have been known to attend service at that Church, because connections in the entertainment industry are more important than the paycheck. Maddie was saving herself for marriage but that didn't mean she didn't get around and found other ways to find sexual arousal with her female paramours, but we'll get to that shortly.

Maddie was a bit taller than Cora, maybe an inch or two. Despite growing up within spitting distance of the beach and in a place where the sun shines three-hundred days a year, her skin was quite pale. She had blonde hair in the most feminine of pixie cuts, not like your typical really short pixie cut, and had blue eyes with dimples on her cheeks. She had larger breasts, D-cups, a fit body; she liked to work out a lot. She had a smaller ass than Cora, but not that much smaller, and was definitely in better shape. She had multiple tattoos on her body, all of which were religious themed to fit in with her persona.

Back to Cora. She was currently dating a man where they met while working at the same firm. His name was Jeff Wan, half Chinese and half Korean. Born in and raised in Monterrey Park, California, Jeff was destined for a life of accounting, as was his father, Lao. His mother was a surgical nurse named Sheila, who was second generation American while Lao was born in Taiwan. Jeff was smart but was a promising athlete, both in Football where he was a wide-receiver in high school and was a track star. He went to the University of Southern California on a track scholarship. Being a man, Jeff was mostly proud of his dong, which he was happy to be of exceptional length contrary to hurtful stereotypes that Asian men not having large penises. He also took care of himself, and was well put-together strength wise. He lived in Eagle Rock in Los Angeles and Cora often spent time in his more specious apartment.

Jeff got around in his day, part of the perks of being a high school athlete; so he and Cora had many evenings and sometimes days just literally fucking around. But they typically engaged in the usual sexual flare: kiss, blow, fuck, repeat. It started in the usual missionary, sometimes side-fuck, and cowgirl, and if they felt like going crazy they would do doggy style. This was always vaginal in nature which is always moist and feels amazing but Jeff, ever the pervert, wanted to spice things up so to speak, and that ends out exposition and onto the story.

Inside Maddie and Cora's apartment, which was messier than one typically thinks of an abode shared by women; sat Maddie on the couch in their living room, scrolling through her bible. Maddie had a gig the next day as an extra on the CW show: Riverdale where she would flirt with the Vanessa Morgan character which would make the Madeline Petsch character jealous because CW's business model is: "add another hot lesbian couple, that'll boost our ratings". Maddie wasn't a fan of the show because it was "too woke" for her taste.

Anyway, Cora entered the apartment, wearing her blouse and long gray skirt underneath a beige duster. She dumped her Prada messenger bag and duster on the floor, along with her heels and made an audible "ugh!" the kind of ugh that screams "notice me", something Maddie was all-too-familiar with.

"Hey, roomie!" The twenty-six year old beamed from the couch.

"Hey Mads."

"You seem annoyed, everything okay?"

"Not really" Cora complained. She hobbled over to their bathroom which was off of the living room.

"O-Okay. Peace be with you" Maddie called.

She knew that couldn't be the end of that. They weren't merely roommates found on Craigslist, they were friends…found on Craigslist. Maddie knew there was certainly something Cora wasn't telling her, and was quite concerned considering Cora was usually forthcoming about her daily foibles, so this was truly a mystery.

Cora appeared moments later from the bathroom, no longer wearing her strong-independent-woman-at-work attire and was instead wearing a very short sleeve t-shirt with 'FARGO NORTH HIGH SCHOOL ATHLETICS DEPT. emblazoned on the front, with Adidas short shorts and UGG slippers, perfect "I hate my life and just want to eat ice cream and die" lounging attire. She took a seat on the couch next to Maddie.

"You gonna tell me what's bugging you?"

"It's personal."

"This from the same chick who disclosed to me that you once pissed on all your clothes when you were sick because you thought your pee was somehow magical and would give you heeling pants. Doesn't get more personal than that." Maddie explained.

"I told you that in confidence, you slut" Cora said, playfully punching Maddie in the arm. "I was four, by the way."

"Seriously, Cor, what's wrong. You can tell me anything."

"I can't, Mads, it's really embarrassing."

Maddie sighed and did a very obvious facepalm and then slid her hand down her entire face. Maddie always had a flare for the cartoonish dramatic. She took a deep breath. Maddie had been around women most of her life, especially when she was trying to be in relationships with them, albeit every one of them ill-fated. She knew this game other women played. It was that game where they want you to guess what's ailing them and continue to prove interest which would validate their feelings. Maddie was tired and didn't want to play the hard-to-get game, so she acted accordingly.

"Okay then."

"Okay then?" Cora reiterated.

"Yup, if you don't want to tell me, I respect your decision."

"That's it, then?"

"Pretty much."

Cora groaned. She sighed and looked off into the distance and Maddie took notice. She was reeling her roommate in. Cora finally turned to Maddie. "Okay, but this stays between us, right?"

"I'm insulted you would even ask such a question."

"Okay. Fine. So, I was at Jeff's after work, I drove him home—"

"When is he just gonna get a car already?"

"Irrelevant" Cora stated. "We were gonna have sex—"

"Oh, it's a sex story, eh?"

"Stop interrupting! But yes, it was about sex. We just started kissing and talking, and talking and kissing but I could tell something was up with Jeff—which is never something you want to see in your boyfriend."

"Dually noted" Maddie said with a giggle.

"So I ask "what's wrong", and he says that he wanted to try and spice things up in our relationship because he thought we were doing the same sexual routines over and over and over again."

Now Maddie was on the edge of her seat. She kneeled both legs on the couch and faced Cora. "Interesting."

"Just please don't laugh, this is serious."

"I'm being serious, continue."

"Okay, so I ask him "well what do you want us to do, I'm up for anything" because you know, I want us to be happy because I love him, you know?"

"Right, of course."

"And he then suggested that we…ugh. I can't even say it."

"Well now you gotta. Tell me!"

Cora did another "ugh", and Maddie was getting a little impatient, however, being that this was sexual, she had narrowed down the list to a few plausible things that would make Cora uncomfortable even to talk about, much less engage in.

"He wanted to…put it in my butt" Cora whispered barely audible.

"What was that?" Maddie asked, chuckling in her head.

"He wanted to put it in my butt" Cora said marginally louder.

"One more time? Still couldn't hear you."

"Jeff wanted to fuck me in the ass, okay!?" Cora threw herself onto the couch, face smushed into one of the many throw pillows.

Maddie wanted to laugh. She had a hunch this would be the case, but wanted it to come right from the horse's mouth. It was kind of amusing. Cora was always weirded out when talking about sex, especially dirty sex, so this was quite the delicious bit of humor to Maddie. Plus, Maddie had engaged in much anal intercourse in her day as previously mentioned she was saving herself for marriage but still wanted to get laid, the easiest, though dubious loophole was butt sex.

She put her hand son Cora's shoulders and gave her a not-so-creepy shoulder massage. "It's okay, Cor. You don't have to be embarrassed."

"Yes I do!" Cora yelled, muffled into the pillow. She turned to face Maddie. "I'm really embarrassed. I've never done anal before!"

"It's really fun. You should try it."

"But it…it's dirty, Mads. You poop from there. That hole is for feces only" Cora whispered.

"Yeah and you piss less than a quarter inch from where you have sex, which is less than a quarter inch from where you shit. Hell, dudes pee and ejaculate from the same hole, but you guys do it all the time" Maddie explained.

"It's still weird. But anyway, we had a huge fight. I may have over-reacted because I was weirded out, and I came right over here. Jeff's been blowing up my phone for like the past hour and I don't know what to tell him."

"Maybe with a yes?"

"No! I'm not gonna let him, or anyone else for that matter butt fuck me. That's too much, it's gross—no offense."

"Some taken. Butt fucking is the shit—poor choice of words, but it feels amazing, and oh-so naughty."

"Says the lesbian Christian" Cora rolled her eyes.

"Hey, I'm waiting for the right gal to scissor with, but for now, my tush is open for business" Maddie added.

"What do I do, really?"

"Do what?"

"What do I tell Jeff? I gotta see him again, we work together, this is bound to come up at some point!"

"Wait-wait, you're positing that as if you can just ghost him and make this go away—simultaneously ending a-what, three year relationship over a question to pop your butt cherry?" Maddie asked.

"Obviously no, but what do I tell him? I get weirded out just thinking about it."

"I'm sorry, how old are you? I get it, it's fucking where you shit, but you're not in the sixth grade, Cor. If it's a hard no, just tell him no, and if I know Jeff, he'll respect your decision because his obvious love for you is way more important that slipping it in your backdoor."

"Wow, you make it sound so easy" Cora made another eyeroll.

"That's because it is easy! Either you're mulling it over, it's a no, or it's a yes, there is literally no other option."

"No, there is never bring it up again and hope Jeff forgets about it forever."

"That's not healthy. And you said so yourself, you guys fought over this, he's gonna bring it up when you see him next."

"Not if I'm happy, and bubbly, and think of a million different things to forever keep Jeff off the subject."

Maddie figured Cora was half joking, but then forgot there was that stereotypical Midwestern prudishness that often ran deep through the Hispanic type-A. Maddie wanted to just say "fuck it" and let Cora stew about her childish antics but they were still friends gosh darn it and she was going to see her friend through this self-imposed difficult time.

"Jeff does not have ADHD, or dementia, or some other condition where you forget stuff, Jeff is a pragmatist, and Jeff loves you. He is not going to let this go because he's not going to let this fester for a future fight, which you know will eventually be the case if there is no closure to it. If you don't wanna take it in the ass, Cor, you gotta let him know. End of story. Tell him not to bring it up again, still not the healthiest option but it gets it off your chest" Maddie explained.

"Ugggggh. Just the thought of saying: "sorry, not interested of taking it in the ass, love you though" is really making me anxious."

"Why exactly? Tear the bandage off, text him no, and call it a night. Seriously, you're a grown woman with a career, a car payment, and a master's degree. I don't see the big deal in all this?"

Cora sighed and just held her iPhone in her hands, with Jeff's text storm opening up. She didn't tap her fingers. Maddie looked at Cora's face and saw the apprehension. She didn't want to tell Jeff. But why?

"Any second now. Come on, you're moving your finger, you're tapping the N, then you're tapping the O. You can do this" Maddie said as if Cora was a child.

Cora didn't respond, however. She merely sighed, threw her head towards the back cushion and threw her phone aside. "Ugh! I can't do this!"

"And why not?"

"I dunno. Jeff's done so much for me, I wanna make him happy, and we could use a little extra romance in our sex life."

"So give it a shot, it's not that bad. Who knows, you might even like it."

It's still gross, and-and-and, it's painful, right?"

"If done the wrong way, but yeah, not gonna lie, it does hurt a little" Maddie explained.

"Exactly! It's gross, it hurts, but it'll make him happy and it is a curiosity."

"I mean, you could try it a little. It's just the two of you. You can start slow, start with fingering and move from there, train yourself" Maddie suggested.

"No!" Cora spat, hitting Maddie with one of their throw pillows. "What if it doesn't work? What if it's awkward afterwards? We'll never be able to undo any of that! If it fails, it could put a rift in our relationship."

"And this isn't? I mean, you're mulling over between never bring it up again and hope for the best or try it and assume it'll fail and let that ruin your relationship. Do you see the conundrum you've put yourself in?" Maddie asked.

"Why is this so hard!?" Cora spurted with an exasperated sigh.

"Life had no instruction manual, except this one" Maddie explained, holding up her bible.

"I wish there was an instruction manual for butt fucking" Cora chuckled.

"Yeah, they'd call it like, the: "Tushy Technique" or some such nonsense like that. It's not like you could have a third party train your ass." Maddie casually added.

Cora raised an eyebrow. She was interested in Maddie's random ramble. "What do you mean?"

"Like, if there was someone out there who could train you to take a cock in your ass so you can go to Jeff and YOU could show him how to properly fuck you. Yeah, yeah that works, because it's super feminist because it puts you in control and he gets to pound you in the butt. Literally everyone wins."

"That's crazy…but, I mean, it could work. I mean you fuck chicks in the ass all the time, right? Wouldn't it be perfect if you were the one who trained my ass?"

"Yeah" Maddie laughed. "You are lucky you met me, I do enjoy a few rounds of lesbian anal sex from time to time, I guess it would be a perfect trade-off" Maddie said, then promptly transitioning to dread. "But that's crazy. You'd literally be cheating on your boyfriend to save your relationship. The irony writes itself."

"Y-yeah. It's crazy, you're right. But…hypothetically speaking, could you—you know, train someone in anal sex?" Cora asked.

"Oh yeah, sex is all about technique, lubricant, and positioning; and obviously the better your health, the longer and satisfying it feels" Maddie explained.

"Huh…" Cora trailed, but got closer to her roommate. "What do you do?"

"What do you mean?"

"Like, what does a lesbian who doesn't use her vagina do sexually, exactly—if it's okay if I ask?" Cora inquired.

"Oh come on, we're like family now" Maddie began. "I like to spank my girls. It warms up their ass a little bit which for my experience helps with the impending anal pain, but results may vary wildly, plus it's hot. Then I like to open their ass up with some fingering to start to stretch her hole out, and if I really like her, I'll service her hole."

"What's that?" Cora asked.

"Oh, I give her a rimjob. Just licking her asshole—but only if she's a good girl. Then I'll start with small dildos after my fingers and work my way up to my strap-on, which is pretty big. And sometimes I'll work in some restraints, whips, stuff like that" Maddie finished.

"Huh. And you've never licked a vagina?"

"Well I have, but that's only when the chick is too horny to care and just wants some loving. Usually they respect me and we just do mutual anal. But that's that."

"Huh" a perplexed Cora mused.

"But like I said, that's crazy. You'd be cheating on Jeff."

"Right. Totally crazy."

It seemed like the two were over the conversation they had that evening…well, Maddie was over the conversation but Cora had other plans. She was intrigued. As much as she had it in her head she didn't want to have anal intercourse, it was such a taboo fantasy that the thought was admittedly a sexy curiosity.

Cora was beginning to take Maddie's half-handed joke seriously. Cora was a pragmatist at the end of the day if not a bit paranoid. On one hand, she was too nervous to have Jeff help her train herself in anal. She assumed he had never fucked a girl in the ass before and knew one screw-up would mean a world of pain for her while Jeff feels nothing. If this taboo misadventure turned out to be a colossal failure, it could strain their relationship. Cora didn't like talking about intimate details and felt like something like this would be too much to either ignore or talk about if it went south. Cora definitely put the thought in her head that she could shit while Jeff was fucking her, something that came to her in a dream that night after watching a John Mulaney comedy special, you know the one.

So, given that, and her openness with Maddie, as well as her experience in giving and receiving anal she felt like the ideal candidate, especially considering it was Maddie who put this thought into Cora's head. Also, Maddie was naturally quirky and awkward, a stark contrast to Jeff's nature which was borderline bipolar. He could go from stoic to animated on a dime. Maddie was also very awkward naturally which contrasted Cora's perfectionist nature, so even if it was a fail, it wouldn't strain their friendship; they could at least laugh about it later.

Moreover, Cora was such a pragmatist, she didn't even care if Maddie was a woman and thus be committing herself to girl-on-girl sex. On one hand, Cora seemed prudish, but her love for Jeff and her efficient nature didn't have time to mull over sexual orientation taboos, and it was the twenty-first century after all, women "experiment" all the time nowadays and it means "nothing." Plus, there was something calming about Maddie's inflexible commitment to Christianity despite her being an open lesbian. It was almost like having some weird form of blackmail if Maddie were to disclose that she had lesbian anal sex with the straight Cora then Cora could somehow expose her as an LGBTQ Christian, which was dumb on two counts: one, Maddie made no bones about the openness of her faith/sexuality and two, it wouldn't even be in Maddie's nature to speak of such an affair…unless it was to her priest.

Cora mulled this over all the next day. She didn't associate with Jeff all day but got a text from him saying: Hey, can we talk tonight? This was followed by the heart emoji and a few others. Cora obviously said yes, finally replying to Jeff's torrent of texts. At Jeff's swanky Eagle Rock apartment, he had put on his best boyfriend chops and made dinner. Cora was very quiet as was Jeff and the two awkwardly reminisced about their day at work and the direction the company was going—it varied from guy-in-an-elevator small talk to work-friends-but-nothing-more small talk. After some wine and awkward silence, Jeff poured himself…and then quickly downed himself another glass of liquid courage and finally popped the question—

"So, can we…talk about yesterday?"

Cora paused, running her fingers around the rim of the wine glass. "What's there to talk about?"

Jeff wanted to bang Cora in her sweet ass, but he was a nice guy and his love for Cora meant far more than banging her in the booty. "I mean, I'm sorry Cor. I-I-I shouldn't have just out of the blue suggested we…we butt fuck."

Cora knew Jeff sort of meant all those right-pretty nervous boyfriend words and just wanted to wave the white flag of surrender to avoid a pointless argument. "It's…fine."

Pro tip: Anytime your GF says anything is fine, that is literally the exact opposite of fine! That means "nothing is fine, I'm still mad at you, but I'm not furious and we are not done with this conversation" Either she wants you to dig and fish for a solution to be emotionally available and listen to her feelings or she wants to figure it out on her own and doesn't want you to worry.

"It doesn't sound fine" Jeff said, going with option one.

"I mean…anal is so dirty, and painful."

"I know, it's just—I dunno I thought it'd be fun and kinky. Something new, you know?"

"No, I know that! I'm not mad that you suggested something new. You just insisted, and it's dirty. That's what I was mad about."

"Right, and I'm sorry. It wasn't my place."

Cora said those words but the more she took a day to think about it the more she wanted Jeff in some form of control. She wanted him to tell her to undress, bend over something so he could pop her butt cherry. That was Cora's problem: underneath this prudish feminist lay a hungry sexual tiger that wanted to be taken, and taken hard. She often had trouble disengaging from the latter to keep up appearances with the seemingly stronger and much more visible former.

But, Cora's brain was also mulling over Maddie's "joke" about training her in anal sex. And Jeff seemed like he would go for it if it meant Cora would spread her cheeks for his cock. All the craziness was swirling itself inside of Cora's brain: her Type-A-no-butt-stuff side verses her hungry sexual side. She was blanking, staring off into space, while Jeff took notice.

"Cor? Are you okay? Cora? Yoo-hoo."

Cora snapped out of it. "Huh?"

"I said: are you okay? You look like a space cadet."

Cora looked for the right response, but was only able to blurt out: "Hey, uh…you uh, wanna hear something funny?"

"Um…I guess, sure."

"I was thinking about it last night, after our fight" Cora began finishing her wine. "I was all upset because you insisted, right? But, I think maybe part of that was just me being nervous, because like, anal is gross, and painful."

"Right and I'm really sorry because I was being selfish and—"

"No-no-no-no-no, don't worry about that, I know that. I thought: "gee, wouldn't it be so simpler if there was like, someone who could train me in anal before we did it?", because that way I'd know what to do so there'd be no pain or grossness."

Jeff laughed, nothing placates your angry GF more than laughing at one of her jokes to help beak the awkward. "Like sex-ed, except you get sex training?"

"Right? So dumb. Like, you know Maddie is into fucking girls in the ass, right?"

"I know! And she brags about it. I've known a few lesbians in my life but I've never seen anyone like her" Jeff chuckled.

"Right, but like wouldn't it be funny—and convenient if she taught me how to do anal" Cora finished, nonchalantly pouring another glass of wine.

Jeff raised an eyebrow. This didn't sound like his girlfriend of three years, this sounded like his girlfriend of three years if she had fallen on her head. Cora was extremely adamant not twenty-four hours before about Jeff never getting his dick near her asshole, and now she was suddenly making a subtle "joke" about her lesbian roommate teaching her how to get ass fucked.

"Wait like, like Maddie like, fucks you, in the ass? With what, like a dildo, or something?"

"Yeah, right. I dunno it was just a joke. But, it would be like teaching me to help us. That way there is nothing awkward and I know what to do, and most importantly, there's nothing to fight about" Cora finished, and then finished her freshly poured glass of wine.

"I mean, you're right that's pretty fucking funny" Jeff chuckled. "Real-life sex ed. That'd be hot."

"Really?"

"No-no, I mean like real life sex ed" Jeff corrected himself, fearing more of Cora's wrath.

But to the contrary, Cora was very interested in Jeff's notion that it would be hot…it almost seemed like…consent? She thought for a moment, and decided to subtly cultivate this devious plan.

"No, you meant it would be hot if Maddie fucked me?"

"No...n-no that's not what I meant" Jeff defended.

"It's okay if it is. Do you really think it would be hot?" Cora asked.

Jeff sighed, still reeling from the previous fight. But he acquiesced and nodded. "Fine, yeah. But like, who doesn't want to watch two girls fuck?" he asked as if this was a good defense.

"No, it's fine, thank you" Cora smiled. "So, it would be hot, that's what you're saying? If Maddie and I fucked?"

"Yeah, it would be hot."

"Good to know" Cora muttered, a smile on her face.

"But, you know, like you said, it was a joke" Jeff shrugged.

"Yeah…right."

Cora had made up her mind, or in her mind, it was made up for her by Jeff. She figured Jeff saying how hot it would be if the two fucked would be enough of a permission slip for her to actually do it. Cora couldn't straight up ask Jeff and make it into a proposition…no, that would be too much, and what if he said no? That certainly made this situation of infidelity more and more dubious. But, Cora figured she could make it up to Jeff later, after all, this was for him.

Dinner was pretty tame after that. Cora made an excuse to leave but left Jeff happily, both on good terms again. Cora made the three hour drive back to her Hollywood apartment, her mind made up. Cora barged into her apartment, where Maddie was busy reading a verse from Genesis. Cora slapped Maddie's bible from her hands.

"Hey! I was reading that!"

"You're always reading that" Cora balked, but then changed her tone. "I've decided to take you up on your proposition."

"Which was?" A confused Maddie asked.

"You know, you know exactly what I mean, Maddie" Cora said sternly…almost sinisterly.

Maddie instantly remembered her so-called "joke" realizing it wasn't a joke to Cora anymore…hence why she needed to be reminded. "Surely you can't be serious?"

"I am serious. And don't call me Shirley."

"Wha-what? Cor! I can't do that!" Maddie pouted, standing up to mean business.

"Why not? You've ass fucked plenty of women. Just another notch to the bedpost."

"No shit, Sherlock, and thanks for making me look like a whore! I meant, I can't do it, because I won't do it, because then YOU would be cheating on your boyfriend! I will not involve myself in infidelity. Commandment six: thou shalt not commit adultery!"

"If I recall correctly, that is for those of us who are married. You see a ring on my finger?"

"It's still a relationship, there's not a chance in hell I'm gonna involve myself in this" Maddie insisted, walking away towards their kitchen.

"No, it's fine, Jeff gave me the go-ahead."

Maddie turned around, and raised an eyebrow. "Really? Jeff told you it's fine that your lesbian roommate ass fuck you, instead of him? Which by the way, was the whole reason we're having this conversation right now."

"Yeah, he said it was fine" Cora lied.

"He does know someone else—that someone being me, is going to fuck you?"

"Yeah, that's traditionally how that works" Cora nodded.

"I-I just can't wrap my mind around this. Jeff is fine with you cheating on him?"

"It's not cheating if he endorses it" Cora reminded her.

"You are aware I have a vagina, you are going to be having homosexual intercourse." Maddie explained, having her first objection answered for.

"Now who's the prude?" Cora coyly asked.

"You're okay with this? Cora, I was joking. You know, a joke. A ha-ha."

"What do you care? I'm hot, my boyfriend said it was fine, and you get some ass. Win-win."

"Because…b-b-b-b-because" Maddie stammered. "W-What were Jeff's exact words?"

"I put it up as a question and he said: that sounds fine, babe" Cora lied.

"Fine…h-h-he's okay with this, really?"

"Yup. He said it would be hot" Not a lie.

"But—but he—you—" Maddie stuttered again.

Cora knew a thing or two about psychology. This was Maddie desperately trying to find an answer against doing this because it didn't fit into her moral code. Cora knew Maddie wanted to fuck her, she could feel it in her stammers. She just needed a little push. Cora smirked.

"Come on, Mads…" Cora smirked before lowering her pants and underwear, revealing a completely shaven pussy. Maddie immediately shut up and her eyes instantly went downstairs. "…You sure you don't wanna fuck this?"

Cora then did a spin move and instantly turned around, revealing her tanned jiggly ass to Maddie's eyes. Hello lady boner. Cora shook her ass for her roommate, practically propositioning Maddie to touch her cheeks. Maddie huffed as she felt herself step closer and closer to her promiscuous roommate.

"You don't wanna fuck me in the ass?" Cora bent down, her cheeks instantly spreading, revealing a hairless crack, and a puckered asshole. "My slutty ass?"

Maddie reached out her hands, but stopped short. She was defeated. If she said no now, Cora would only persist. She knew Cora. And if Jeff did in fact okay this, which technically he didn't, then what harm could it do? Maybe Maddie could do more volunteer hours down at the church. She sighed, at least she would get some.

"Fine"

Cora stood up and faced Maddie. "Really?"

"But we're doing this my way. Okay? You are my student, and you do as I say" Maddie demanded.

"Right, of course. No problem" Cora effusively promised her. "So, how does this work, exactly?"

"First, go to the CVS down on Cahuenga, and get the following items: disposable enema, water soluble lube, and a beach towel of some sort."

Ever the pragmatist, Cora got out her iPhone and opened a page of notes, typing down the very short list. "Got it, what else?"

"That's it."

"I'll be right back. Oh, thank you, Maddie. Thank you-thank you-thank you!" she gave Maddie a hug.

"This isn't going to be romantic, understand?" Maddie warned. "Strictly teaching purposes."

"Exactly. That's what I want."

"Fine, I'll be here when you get back" Maddie nodded.

Cora pulled up her pants and headed for the door, but stopped short. "Is there a particular brand of disposable enema that you prefer?"

"Cora, I'm already not feeling this, please don't piss me off!" Maddie fumed "It's a cock-sucking enema! Any one will do!"

"Right, sorry. I'll be right back!" Cora grabbed her keys and left, letting the door slam behind her.

Maddie groaned, wondering about the consequences of what she just agreed to. She did some pondering, some soul searching, and lots of praying. I mean lots of praying. In the interim she had gotten out some toys to train Cora. There was a pink polka-dot vibrator, a pink limpy dildo, made to be wall mounted, and of course, Maddie's massive strap-on cock, which was about ten inches long and nearly three inches round. Maddie already wore the harness over her clothes. From her room, Maddie heard the front door slam. She walked out to see Cora with multiple CVS bags.

"What the hell? I told you to literally get three things!"

"I-I-I panicked, so I bought every enema they had, and like three bottles of lube, and five beach towels, this Pokémon one was the softest. I wanted to go for soft, right?" Cora asked.

Maddie did a face palm. "This is already a disaster" she muttered to herself.

"So, what first?"

"Take an enema, and follow the directions. This is so you can get all the shit out of your rectum so my dildos, and more importantly, so Jeff doesn't get a brown dick."

"Eww."

"Yeah, gross right? Still interested? Cause this is how you do it properly."

"No. Being grossed out is what led me to this in the first place. I will…clean out my asshole" Cora said with a slight stammer.

Cora dropped the bags and went to the bathroom with one enema. She took off her bottoms and looked at herself in the mirror. She opened the enema while a quietly amused Maddie stood in the doorway of the bathroom. Cora removed the rest of her clothes, her cute and thick body on full display. She turned to Maddie. "You're not gonna take your clothes off?"

"Don't need to. This isn't romantic, remember?"

"Right-right. Of course."

After carefully ignoring the instructions, and gently using the tip to lube up her hole, Cora shoved the enema inside of her ass and squeezed the bottle of the warm-ish sodium solvent into her rectum. "Whoa, that feels weird."

"It's gonna get weirder, I promise you. Now once it's all in there, clench your cheeks, and fart it out into the toilet" Maddie ordered.

"Got it."

Cora did as directed, and Maddie smirked watching Cora, with her butt cheeks clenched, hobble over to the toilet. Maddie walked away while Cora relieved herself so as not to make it weirder. "When you're finished, use some soap and wash your sphincter!" Maddie called.

"Can do!"

"I'll be in my room, waiting."

Maddie took the soft towel Cora procured and paid it out on the side of the bed, with the bottle of lube at the ready. After a few more moments of waiting and several toilet flushes later, a nervous Cora appeared in Maddie's doorway, very naked. Maddie could see Cora eye up her instruments of anal torture.

"So, all those are going inside of me?"

"Along with these" Maddie held up her right hand and shook her digits. "Like I said: it's easier if you start out small…" she gestured to her index finger. "Then finish large" she pointed to the monster strap-on cock on the bed.

Cora took a deep breath. This is what she wanted, right? She wanted Maddie to train her asshole so Jeff could also enjoy it, right? So everything would be less awkward…RIGHT? All this was finally starting to hit her as the adrenaline of taboo was wearing off and the impending ass fucking which Maddie warned her against was finally setting in.

She made her peace. This was for their relationship…but also, there was the nature of having her quirky roommate fuck her that kind of turned Cora on a little bit. Maybe there was something to letting your wild side show more instead of your Type-A side? Or, this is what she gets for letting her wild side loose? Either way, she purged all those thoughts from her mind and approached Maddie.

"So, now what?" Cora asked.

"Like I said, first I like to spank my girls, takes their mind off a plastic and silicon dick about to be shoved into their asses. Lay over my knee. Make sure your booty is sticking up" Maddie ordered.

Cora nodded, and sauntered over to Maddie. She bent down and laid herself out onto the bed and over Maddie's knee, making sure to bend her body so her cheeks stuck right up in the air, completely exposing herself.

"If you do this with Jeff, he probably has a stronger arm than I do, his'll probably hurt more. Just tell him to go half-speed. We'll start slow."

"Okay" Cora took a deep breath.

Maddie raised her hand but first got a good look at Cora's rump staring at her in the face. The blonde licked her lips, but then shook her head, desperately not trying to make this experience romantic for either of them.

She lowered her hand down to a more manageable level and patted it down on Cora's tush, causing her skin to vibrate and her legs to gently spasm. Maddie raised her hand and did it again, then a few more. She could hear Cora chuckle.

"What's so funny?"

Cora looked back at Maddie. "You spank like a girl" she cooed.

Not wanting to be outdone, Maddie lifted her hand up high and slammed it down on Cora's rear. "How was that!?"

"Oh yeah! Much better."

Maddie continued apace, laying a beatdown onto Cora's ass. She could see little spots of pink forming a handprint on her cheeks. Maddie continued her onslaught of spankings to Cora's ass, eventually alternating between each cheek to evenly disperse the color.

"Yes! Spank me, Maddie!"

"Stop making this weird! It's not romantic, remember?"

Maddie laid harder smacks onto Cora, while the Latina relished in someone beating her ass. "Call me a bitch" Cora moaned.

"You're a bitch" Maddie deadpanned.

"Yes! Beat me" Cora begged.

Maddie slammed her hands onto Cora's beautiful ass cheeks. She stopped once she saw a perfect shade of red in the middle, with a pinker circle around the outside of her booty. Maddie wiped some sweat from face.

"Okay, you're good" Maddie panted, helping Cora get off of her. The Latina rubbed her sore tushy and stood obediently at attention. Maddie figured Cora wasn't going to give up so easily. "Alright, get on all fours, over the towel. Get your ass as close to the edge of the bed as possible and stick your face onto the bed."

"Face down, ass up. Got it" Cora nodded.

Cora crawled onto Maddie's bed and took the desired position, spreading her legs out and making sure her ass was completely spread apart. Maddie couldn't take her eyes off her roommates gorgeous rump. She snapped out of it after taking the bottle of lube and oiling up her right index and middle fingers. Maddie knelt down, eyeing up Cora's exposed asshole. Boy did she want to rim her, but that was just too romantic of a gesture…but it took all her strength not to, especially considering she didn't think Cora would care too much.

"Alright, I'm going to loosen you up with my fingers, this shouldn't hurt."

"Okay Maddie…I-I'm ready" Cora said a bit apprehensively.

"Are you sure?"

"Yeah. Finger me."

Maddie sighed and lined up lubed up digit over Cora's very clean asshole, first circling the rim before gently sticking it inside. Her sphincter offered little resistance as it was only one finger. Cora took deep breaths as Maddie slowly pushed in and out.

"You feel okay?"

"I'm fine."

"Okay, you're doing great, Cor."

Maddie swirled her finger inside of Cora, trying to lube up her insides for the anal shenanigans to cum…see what I did there? Maddie slid out and slowly added her middle finger to the mix. This was met with more resistance from Cora and Maddie quickly pulled out of her, leaving her asshole puckered. "You okay?"

"Yeah. I'm fine" Cora panted.

Maddie nodded and continued. She went slower this time, adding both fingers at once, and after a few thrusts with only her fingertips, her sphincter opened up and Maddie got them both inside. She swirled them around, scissoring her fingers to help stretch out Cora's rectum.

"Ooh, that's good" Cora smiled.

"The first few thrusts are always the hard part, but you should be more stretched out now. Are you ready to move on?" Maddie asked. "Cause the dildos are up next…unless you want me to fist you, but I DO NOT recommend that for amateurs" Maddie insisted.

"Uh, sure. Yeah" Cora panted.

Maddie continued with a few more thrusts with her fingers. She was admittedly lost in Cora's beautiful booty, especially considering she was literally begging Maddie to fuck it. She slowly pulled her fingers out. She got her vibrator, and drizzled some lube on it.

"Okay, lay on your back."

"Why?" Cora asked.

"Because it'll be easier to get inside of you. It will not be nearly as painful of having to push it down. Now I have to push it up. Your rectum will thank you" Maddie explained.

"You're the expert."

Cora shifted her body and laid on her back, with her ass on the edge of the bed, she raised her legs and spread them out. Maddie knelt down again but this time she froze. She had a perfect gaze at Cora's pussy. It was perfectly shaven…and it was getting moist, glistening from the lights shining on it from the ceiling. Maddie blushed.

"My eyes are up here, Mads" Cora smirked.

"Sorry. It's just…you're so fucking hot, I-I gotta admit. God, I wish you were single."

"I thought we were just training?" Cora raised an eyebrow, breaking Maddie's tough good-Christian-girl defenses.

"Uh-we-we are, right. Okay."

Maddie got the lubed up tip of the vibrator against Cora's awaiting booty hole. She swirled around the sides to tease her before gently pushing it in. It was much larger than her two fingers, but she was still open enough to make this much easier. Plus laying on her back was a huge plus.

"Oh, yeah. Ohhhhh, so that's what this feels like?" Cora huffed.

"You ain't seen nothing yet" Maddie assured her.

Maddie gently pushed the dildo in and out of Cora's ass, as it became more accommodating to the anal invader. She twisted the black cap on the back and started the vibrations, and Cora practically came.

"Oh fuck, yeah! Wow!"

"You've never vibrated yourself?" Maddie asked.

"Not in my ass! Oh, that feels so good!"

Maddie smiled as Cora was clearly enjoying herself. She liked being naughty with her female conquests but this was different. There was a bit of guilt. Maddie never really accepted that this was okay even with Jeff's consent which was an ironic lie. But Cora was too hot for her to handle.

She stared into Cora's pussy. It was the perfect vagina. It was the vagina of Maddie's wet dreams. It took all her strength not to shove her lips onto that pussy and continue to dildo Cora's ass.

She was interrupted by Cora's right hand, where she shoved two fingers over her clit and furiously rubbed. The two pairs of eyes met. "I'm sorry. I-I feel so good" Cora hissed.

"That's okay, you should be feeling good" Maddie assured her.

She continued to ram the dildo up Cora's butt, watching her friend and roommate masturbate in front of her. She slammed the dick into Cora, watching her feet writhe and shake from all the pleasure. Cora was moaning now. These weren't soft moans either, these were loud moans of sexual explosion.

"You like this? You like getting fucked in the ass?" Maddie asked.

"Yes! Oh yeah! God, this is what I've been missing!" Cora moaned.

Maddie smiled, she pulled the vibrator out of Cora and tossed it aside. Cora kept on masturbating as Maddie stood up, moving to her pink limpy wall-mounted dildo before drowning it in lube.

"Oh God! What's next? What's next?" Cora panted.

"Kneel on the bed, and bounce your ass on this dick" Maddie demanded. "It'll be bigger, but I think you can take it."

Cora nodded furiously. She got up and turned around on the bed, spreading her legs out, and using her hands to spread her ass cheeks apart, dripping in lube. Maddie planted the dildo right under Cora's asshole and Cora slowly sat on it.

She winced, trying to force it past the opening of her sphincter. After a false start or two, the dildo went in, and gravity did the rest. Cora fell onto the dick as it filled her rectum up. Maddie readied her big strap-on cock as Cora bounced her booty on the dildo.

Maddie hopped on the bed and faced Cora. "Smack me!" Cora demanded.

"No" Maddie said. "I hope you're ready for this dick" she pointed to her strap-on.

Cora nodded as she continued to bounce her ass. "Oh yeah! I'm so ready!"

"Good, cause we're not stopping until you cum. I think you can handle it, wouldn't you say?"

"So ready! I want you to fuck me, Maddie! I wanna be your little bitch!" Cora shouted.

"No you don't. I look nice on the outside but I'm vicious in bed. Just imagine that's Jeff's cock your bouncing your butt on."

"I am! Oh fuck yeah! Oh yes!"

To prove this, Cora sat all the way down on the cock, her ass touching the fake testicles at its base. Cora was sweaty and panting. She was practically begging for that cock to be shoved inside her asshole.

"Okay, let's do this" Maddie insisted.

"Fuck yeah!" Cora got off the dildo, and watched the lubed up mess fall on the towel.

"Doggy style, bitch" Maddie ordered.

Cora did as told and got in the doggy position, sticking her ass on the edge of the bed. Maddie stood behind her and smirked, her wild side now starting to take over as she watched Cora's hole pucker and gape from being fucked in a variety of ways.

"I'd say your butt cherry has been thoroughly popped, but now it'll be at the hands of my hips" Maddie smiled.

"Fuck me, Maddie" Cora begged. "Fuck my slutty ass!"

"Well, you asked for it."

With no warning, and no foreplay, Maddie shoved the dick inside of Cora's awaiting asshole. The force nearly knocked Cora onto the bed. Her gaping asshole accepted the dick right away and Cora threw her hand behind her and rubbed her pussy.

Maddie pulled out, and pushed the dick back in, slowly thrusting as her rectum was stretching itself out to accommodate the large cock. Cora was in pleasure heaven, she couldn't even believe what she was missing all these years.

"Oh yeah, oh yeah, oh fuck!"

"Hmm, you really like it in the ass, don't you Cora?" Maddie asked.

"Fuck yes! Fuck me like a bitch!" she demanded.

"You were my bitch two dicks ago" Maddie sneered.

She picked up her pace, wanting so badly to throw her clothes off. Eventually it was getting too hot and Maddie threw off her shirt, and bra, revealing her tatted up body and large tits shaking as she thrust the cock in Cora's booty.

Cora continued to masturbate, getting pretty close from the constant ass fucking and Maddie's strict orders. She wanted to cum so badly now. Her ass was completely open, and she had a seemingly endless amount of stamina.

"Pound my ass Maddie!" she begged.

Maddie grabbed Cora by the hips and thrust her entire body into the Latina. Her ass cheeks bouncing off against Maddie's crotch as the entirety of the dick would go in and out of her. Maddie nearly fell on the bed from her only hand holding her up nearly giving out. Her entire body was in this euphoric stage of pleasure.

"I bet you wanna cum?" Maddie asked.

"Oh yes! I wanna cum so badly!"

"Think of Jeff. Think of Jeff fucking you!" Maddie huffed. "Think of his dick cumming in your slutty butt."

"God! Oh I want that! Oh I want it in my ass! I love it!" Cora moaned. "I love it!"

"Good!" Maddie hissed.

"Oh God! I'm close, Mads!" Cora huffed. "I'm gonna cum! I'm gonna cum!"

Maddie shoved the entire length into Cora's butt and Cora finally exploded in a climactic orgasm. She muffled her face into the bed to silence the earth shattering screams. Maddie could see Cora's pussy dripping juices onto the towel.

Her knees feeling weak, Maddie fell on top of her. She turned her head, almost in a drooling phase while laying on top of her apparently bi-curious roommate. The two caught their breath after a few moments.

Maddie quickly got a hold of herself and got up, slowly pulling the shaft out of Cora's rectum and she watched her hole gape. Maddie slowly dropped the harness and laid on her bed. Cora laid next to her. She went in and hugged Maddie, and the blonde blushed.

"That was fucking amazing! Thank you, Maddie."

"I gotta admit. I've fucked a few women…but none moaned like you" she smiled.

"That was the best. I need more. I need more right now! I-I gotta go see Jeff!" Cora leaped from the bed and into the other room where the rest of her clothes were discarded. "Fuck it, I'll wear comfy clothes!"

She ran into her room as Maddie got off the bed. "You sure? Right now? Your ass is probably sore as fuck."

"I don't care!" Cora yelled, throwing on some comfortable shorts and a shirt. "This is what I've been missing, Mads! I love anal! I want it in my ass every day! I can't believe I went so long never experiencing it! Now I believe!"

She ran and gave Maddie a kiss on the cheek. "That-that's good."

"I'll be back later! I'll give you all the deets!"

"Wait-wait!" Maddie stopped Cora before she was halfway out the door. She ran back into her room while Cora followed her. From a dresser, Maddie produced a pink butt plug.

"A butt plug?" Cora asked.

"It'll keep you loose. Trust me, you'll thank me when Jeff's dick isn't stretching your ass out."

"Perfect!" Cora turned around and dropped her pants. She spread a cheek out, as her hole was still puckering. Maddie lubed the plug and slowly inserted it into Cora's ass, getting it down to the base, and watched her hole close.

"You're good."

"Thank you!" Cora pulled her pants up. She tried to run but realized this was difficult with a plug in butt, so she waddled, and grabbed her keys. "You are the best Craigslist roommate I could have asked for!" she blew Maddie a kiss before closing the door behind her.

Maddie sighed. She fell on her bed. She had a lot to think about. But at that moment, all she really wanted to do was cum. She looked up at her light and ceiling fan as she shoved her hand down her shorts and masturbated furiously. But little did she know of the slutty monster she just created…

But that was a different problem for a different day.


	2. Type-A for Anal

**Summary for the Chapter:**

> Now craving Jeff's cock in her ass, Cora confronts her boyfriend and the two have their first anal shenanigans while Maddie mulls over what she had just done, unable to orgasm from her supposed shame. She and Cora know this isn't the end of their booty play.

While Maddie laid in a pool of hers and Cora's sex sweat, Cora hopped in her car, and sped her way down Franklin ave, heading for the miserably decaying 101 Freeway. Cora had a hard time adjusting for a comfortable place in her car to sit as the butt plug made finding a good place to sit your booty almost impossible.

But she loved it. Cora couldn't believe how much her life changed in a very short period. She became so disgusted with anal and in the course of hardly forty-eight hours, she craved it. She wanted to be fucked in the ass and some part of her didn't care who it was bending her over and pounding her booty.

Cora couldn't wait to spread her cheeks for Jeff to shove his dong into her tush, assuming he still wanted to. She knew he would, especially considering how Jeff's mind works. Sure, there might be some mental finagling considering Cora's formerly firm stance on butt fucking and maybe he would think this was a test, but perhaps he could be placated?

Her Type-A brain a-workin', Cora passed a sex shop near the freeway entrance. She had an idea in order to keep Jeff from asking too many questions and they could just get right down to fucking. She smirked, and found a place to park near the shop.

Back at the apartment, Maddie laid on the bed, masturbating furiously. She had taken off the strap-on harness and vigorously rubbed her clit, no effect. She then stripped away at her shorts and panties and tried the same. This was better but not good enough.

After many ill-fated attempts at orgasming, Maddie gave up and threw her hands over her face in defeat. She let out a heavy sigh and stared at her instruments of anal torture next to her, all of which were just shoved up her hot roommate's asshole.

Defeated and dejected, Maddie went to the bathroom and washed her face, looking at herself in the mirror and she wasn't a fan of the blonde lesbian staring back at her. She could hear each droplet of water fall off her face and onto the porcelain sink. She could hear every decibel in the automatic bathroom fan overhead, and that faint ringing sound from the fluorescent light above on the ceiling. Now completely naked and very ashamed, Maddie let out a defeated sigh. She couldn't believe what she had just done. She had fucked her apparently bi-curious roommate who was in a relationship with someone else. Maddie didn't know who she was more disappointed at: Jeff for okaying this backdoor debauchery; which little did Maddie know he actually did no such thing, or Cora, who had capitulated her so-called "joke" into reality.

But of course, Maddie really had no one else to blame but herself, giving into her carnal desires in the supposed name of science. It's not like Cora held a gun to her head or threatened the blonde with any such ultimatums for not butt fucking her, but yet Maddie gave in anyway with not a ton of resistance. She continued to look at her face in the mirror before turning on the shower, hoping to relieve her pain and sorrow she was imposing on herself.

Back over to Cora, she had made her way to the Two, a freeway spanning the Los Feliz area of LA all the way over to the city of Glendale slightly northeast. Smack dab in the middle of all that was the Northeast side, where Jeff lived.

She had with her, her items she procured from CVS, but also two items from the sex shop. Cora smiled, being so proud of herself she was shopping in public with a butt plug inside of her and no one was the wiser. That turned her on so much. So much in fact, that Cora slid a free hand underneath her shorts and started to rub her clit as she drove at freeway speeds towards Jeff's apartment.

The song DLZ by TV on the Radio played over Cora's attached iPhone to the car's stereo. It was a seemingly perfect song to go with her rhythm of masturbation while she drove. In retrospect, Cora first thought of Jeff and how much she wanted him to bend her over and pound her ass.

But, her mind started to drift. It drifted to her recent sexual experience with Maddie and how much she enjoyed being her little lesbian anal slut. It was perhaps one of the hottest experiences of her life. Mostly because of the taboo nature coupled with her newly found love of ass fucking, and because there was something commanding in Maddie's voice that was just such a turn on.

Cora bit her lower lip. "Yeah Maddie. Fuck my ass. Yeah. Oh yeah" she moaned. "I'm such a bad girl, fuck me. Fuck me hard."

She continued this routine, switching back and forth between her and Jeff until the idea popped into her head that only nineteen year old frat boys think about: threesome. She KNEW Jeff would be down for that, but Maddie would of course be the one to object. The obvious: she wasn't interested in Jeff as she was gay, but almost more importantly was her devotion to her faith. Cora sighed, figuring this would be a pipe dream.

But, the midwestern Latina had bigger fish to fry. She found a questionable parking spot near Jeff's apartment. She got her bags of sexual things and ran up to Jeff's second floor bachelor pad. Inside, Jeff was robed up, fresh from a shower, and was enjoying the few puffs from a freshly rolled joint, because cannabis is legal recreationally in California. Jeff was wasting his time, watching the soon-to-be-classic comedy The 40 Year Old Virgin on his TV. In Jeff's stoned stupor, he never locked his door after Cora had left, and became instantly paranoid when his horny girlfriend in her pajamas barged into his apartment.

"What the fuck!?" Jeff shot off his couch. "Oh Cor, Jesus, you scared the fuck out of me"

Cora said nothing. She bit her lip, dropped her bags and ran into Jeff's arms, immediately making out with him with the more muscular Jeff held her up. While their tongues explored each other's mouths, Jeff was at first confused, assuming this to be a pot induced hallucination, then remembering that's silly. He gripped Cora's ass cheeks for better support while Cora wrapped her arms around his waist.

Jeff's dick immediately tent poled from inside his robe, which Cora definitely felt. Cora took her tongue out of Jeff's mouth and bit his lip before moving onto his neck. After some moans from Jeff, the two looked into each other's eyes.

"Hey babe" was all the high Jeff could mutter. "Sup."

"Take it off" she ordered.

"Wait, now?"

"No, tomorrow. Yes, now! Take it off!"

Jeff immediately undid his robe and his dick flopped free. It was an impressive nine inches, not nearly as girthy as Maddie's fake strap-on cock, but definitely a dick Cora was happy to have ram her. Cora jumped back into Jeff's arms and the wo made out while Jeff haphazardly stepped around his apartment in order to keep his balance, as his knees became weak from having to suddenly prop up his girlfriend while being high as fuck.

During this hilarity, which was much funnier than sexual, Jeff backed into a stereo, playing selections from his iPhone. The first song playing was Woke Up This Morning, by Alabama 3. Jeff managed to walk them into his room where he finally fell and sat on his bed, still propping Cora up while the two kissed each other. Eventually they released.

"There's something oddly sexual about The Sopranos theme song" Jeff said, remarking the selection currently playing.

"There's also something sexual about butt fucking" Cora hissed, biting his lower lip again.

Jeff was confused by this. A few hours ago, Cora was anal sex's strictest opponent, and now openly called for some of it.

"Wait, what?" Jeff asked. "Are you fucking with me, babe? Be real. I'm kinda stoned."

"I know" Cora said, licking his face. "But I'm serious. I want you to fuck me in the ass, and I want it now" she begged, using a free hand to slowly jerk off Jeff's erect dick sticking up from him sitting on the bed.

"W-wait, now?"

Cora got right up in his face. "Now" she demanded, before kissing his neck again.

"W-wait, wait" Jeff moaned while Cora left hickeys on his neck. "I'm confused. You like, didn't want it in the ass? Now you want it…in the ass?"

"Yeah" Cora said matter-of-factly.

"Hey, Cor. I don't think you understand, I'm like really high, I don't think I can really process—" Before Jeff could continue his stoned slurring, Cora slapped him in the face. "Okay, ow! The fuck?"

"Quit being a bitch, and bend me over!" Cora hissed.

She got off of Jeff, who used one hand to rub his cheek while using the other hand to jerk off a little bit to keep the wood going. Cora then stripped away her shirt before turning around and seductively tearing off her pants, and in doing so revealing the pink butt plug inside her delicious ass. Jeff's dick immediately hardened while his mouth became slack-jawed.

"What the fuck?"

Cora smirked and turned over to him. "Let that process, while I return." She went into the living room to get the things she brought with her while Jeff sat on his bed, confused but also ready to pound his sexy yet seemingly contradictory girlfriend.

Back over to Maddie. She was in the shower, not exactly showering, but was furiously rubbing her clit, while using her free hand to prop herself up on the off-white tiled walls which were riddled in soap scum and possibly mold. While doing so, she was also listening to music over her iHome, Casting Such A Thin Shadow by Underoath was playing. She grunted while she rubbed herself.

Maddie couldn't get over how hot it was training Cora's ass. She still felt a fair bit of guilt and shame over it, but this was slowly overlapping with the sexual aspect and she wanted to do it again and again. She figured Cora wouldn't object, but Maddie desperately wanted her to.

Her horny side was something Maddie tried to keep under wraps largely due to her faith, but it would resurface from time to time. What she really felt was shame for contributing to Cora cheating on her boyfriend. Once again Maddie couldn't rectify masturbating despite how horny she was.

"You like in your ass, you little slut?" Maddie panted. "Take it. Take my cock! Beg for it, whore. Beg!"

Maddie then started to cry. It started with just a few tears before turning into a wailing moan, being washed away in the lukewarm shower water. After realizing she couldn't continue, Maddie sat in the back of the shower, head in her knees as the water cascaded over her body. She knew this wouldn't be the end of Cora's demands to have her ass fucked, but Maddie had to be the stronger one. She needed to put a stop to it…but how? She sighed, and wiped her tears as the water continued to wash over her.

Over at Jeff's, the song had changed to Hot Girl Bummer, by Blackbear. Cora had laid out her towel and gotten her lube, and showed off the two toys she procured from the sex shop on her way over. The first, was a pair of pink fuzzy handcuffs which Cora dangled in front of Jeff. In the other hand was a heart shaped paddle, obviously used to spank her with. In the middle of the heart in sunken in letters was NAUGHTY GIRL. Jeff's cock stood at attention while he had to close his mouth in order to keep himself from drooling like a babbling idiot who never saw a naked woman before.

"Whoa" was all Jeff could utter.

"First, I want you to spank my naughty ass" Cora demanded. "But I want you to restrain me."

"Uh, okay" Jeff nodded.

He got up and Cora handed him the cuffs. She put her hands behind her back while Jeff kissed her neck, before locking her wrists in between the fuzzy cuffs. Once they were secure, he gently pushed Cora over to the bed and she fell over on it. Jeff took the paddle from his girlfriend and raised it while Cora moved her wrists away from her ass.

"You sure you want this?" Jeff asked.

"Are you gonna keep being a little bitch or are you gonna spank my ass, already?" Cora taunted him.

Jeff nodded, taking the hint and he came down hard on Cora's ass. The girl moaned, especially as Jeff hit the butt plug too, it got shoved a bit more into her asshole. Cora smirked after the pain subsided.

"How was that?" Jeff asked.

"Like getting spanked by a grandma. Fucking hit me!"

Again, Jeff raised the paddle but didn't hold back this time, and came down hard on his girlfriend's cheeks. Cora winced, but was much more satisfied this time. Jeff continued to lay waste to Cora's cheeks.

"That's better! Now spank me! I'm a bad girl! Punish me!" Cora begged.

Jeff laid the paddle down on her ass again, continuing to make Cora's amazing ass cheeks red. Cora started to move her legs as she was feeling the pain from being spanked as tears started to roll down her eyes.

Jeff stopped for a moment to gaze upon his work, Cora's ass was now a lovely shade of pink, with some bruises not withstanding from Maddie spanking her an hour or so ago, but Jeff merely assumed those were from him. Her ass was also red hot from the paddle.

"Good boy" Cora hissed. "Now, let's get that cock nice and wet"

She turned around and spread her legs, revealing her perfect dripping wet pussy. "Oh yeah" Jeff moaned.

He got in front of her and shoved his hard cock right inside. Cora moaned as his rod filled her out. He latched his arms onto her from under the bed and thrust his dick inside her pussy. Cora moaned and kissed his neck with furious passion.

"I want you nice and wet for my asshole" she huffed.

Jeff liked the sound of that. Cora wrapped her arms around Jeff's waist again and he picked her up, fucking her standing up. Cora moved her hips while her wrists were still bound behind her. Cora hissed while Jeff pounded her pussy.

Cora really wanted to profess that it was Maddie who popped her anal cherry, thinking this would turn Jeff on, or at least make him want to punish her further. But she withheld this information as Jeff was already skeptical going into this.

Instead, she moaned while Jeff went to town on her pink pussy, his dick filling her hole out like a jack hammer. Cora could feel herself getting close but didn't want to waste this opportunity to cum while getting ass fucked again.

"Okay, okay I'm ready!" she moaned. "I wanna bounce my ass on you big, thick, cock!"

Jeff lifted his bound girlfriend off his cock. He kissed her again and a little bit on the necks while fondling her exposed breasts, giving each tit a little love before sitting on the edge of the bed. He took the discarded bottle of lube and greased his dick up before Cora waddled over to him. She kneeled on the bed, straddling his cock. Jeff reached behind her ass and got a grip on the base of the butt plug. He pulled it out of her while Cora winced, not knowing how that was gonna feel like. Her hole gaped. While Jeff used his free hand to tap his cock against her anus.

"Shove that toy in my mouth" Cora ordered.

"What?" a stoned Jeff asked.

"Do it!"

Jeff nodded, he reached in front of her. Cora opened her mouth, while he stuck the plug in. Cora got a taste of plastic and lube, as well as musky sex sweat. She enjoyed the taste. She nodded for Jeff to go ahead.

Jeff was now a bit apprehensive, especially considering Cora's earlier objections which put the two in this situation. But, not wanting his girlfriend to call him a little bitch again, he put his dick against Cora's asshole, and the Latina took a deep and slow breath as she sat her ass down on it, while Jeff kept his dick steady. Now, the song playing appropriately was The Man by The Killers, a fantastic song for intercourse.

Cora forced his cock into her asshole, which filled her rectum up as her sphincter spread out. She fell on the rest of Jeff's nine inches and blushed. She moved her ass around as Jeff fell onto his back, mesmerized that he was ass fucking his hot girlfriend.

"Holy shit!" he moaned. "Oh that feels so tight!"

Cora smiled, she liked the sound of that, especially considering it was true. As she moved her ass, Cora started to actually bounce on Jeff's dong. They were slow at first and without rhythm as Cora was not used to this sort of fucking. Also, not having the use of her hands made it a bit more difficult.

She started to get the hang of it as her booty bounced up and down, her ass filling out nicely for Jeff's big cock. She looked down at Jeff, almost drooling from butt fucking her, though she was in part chalking it up to his stoned state of mind at that moment.

Jeff reached his hands out and grabbed Cora's cheeks and helped control her bounces while she fucked herself. She grunted while Jeff groped and occasionally smacked her cheeks while she got her tushy fucked. Jeff moaned.

"Oh yeah. Oh baby I've wanted to do this for so long."

Cora nodded and continued her motions on his cock, sometimes going back to shaking her booty with his entire length inside of her. Jeff's groans grew louder, and probably could have awoken his neighbors, but he was in too much euphoria to give a shit.

"Fuck yeah! Fuck that's good!"

Cora finally stopped and motioned for Jeff to get up. He nodded, and slowly lifted Cora off of his cock, her booty hole gaping while Jeff's cock leaked some pre cum. Cora then let her body bend over the bed, and Jeff did the math from there.

"Oh, is this how you want it?" he asked seductively. Cora spit out the plug.

"Finish inside of me!" she begged. "Fuck me hard!"

Jeff nodded and stood up. He spread her cheeks open with his hand, and without skipping a beat, shoved his cock right into Cora's awaiting hole, spreading it out instantly. He moaned as he fucked her hard. The song then changed to Lights On by Big Grams.

Cora moaned too. Simultaneously thinking of Jeff and Maddie bending her over this bed and taking turns at her ass. She liked this anal attention. She craved it. She shook her ass while Jeff nailed it from behind.

"Yeah baby! Make me your anal whore!"

"Oh really? You like getting ass fucked, huh?" Jeff asked with a smack to her right cheek "Huh?"

"Yes! Yes, I want it in my ass! I want you to fuck my slutty asshole every day!" Cora bagged.

"I can arrange that!" Jeff brimmed, gleefully accepting her proposition.

He continued to nail his girlfriend in her booty, his dick now very well acquainted with Cora's rectum. His thrusts were so much, his crotch was meeting with Cora's cheeks, and his balls slapping into her pussy, making his sack wet with Cora's dripping juices.

"Fuck me baby! Make me cum!" Cora begged. "I wanna cum so fucking badly!"

"I'll make you cum!" Jeff promised with gritted teeth.

He was starting to get close. In his stoned state Jeff was a sexual animal, and could have probably gone another twenty minutes or so, but this experience really turned him on and it wouldn't be long before he exploded into Cora's asshole.

"God! I'm gonna cum!"

"Me too! Cum in my ass, baby!" Cora begged. "Cum in your little anal whore's ass!"

Jeff wiped some drool away from his face and continued to pound Cora's asshole, he watched his dick split her cheeks apart while Cora laid helplessly with her wrists bound to the handcuffs. He felt that feeling in his balls. He was gonna cum hard. He grunted as he made one final thrust into Cora's booty. Cora's rectum tightened as she was about to cum too. The two moaned pleasurably.

"I'm gonna cum!" Jeff yelled.

"Me too!"

Jeff held onto Cora's hips as he let out a mighty roar. Hot shots of cum blasted themselves into Cora's bowels, coating her insides and filling up her rectum while Cora simultaneously came, her body writhing from her pussy contracting.

"Awwww!" Jeff moaned.

"Oh fuck!"

Jeff continued to shoot load after load of jizz into his girlfriend's rectum. After a time, the two finished, and Jeff could feel his dick empty out the last drop. He pulled out, his cock coated in lube and his own juices. He watched as Cora's asshole gaped and slowly, a stream of cum leaked out, with more gushes with each contraction.

"Oh baby, look at that." Jeff moaned, spreading her cheeks to admire his work of planting his seed in her tushy.

Jeff unlocked Cora's cuffs and she clenched her ass cheeks, heading to the bathroom to blast Jeff's load into his toilet while Jeff haphazardly cleaned up the mess in his room. He couldn't have been more satisfied, not realizing the events which brought them to that point.

Cora soon returned and pounced into bed with Jeff, making out with her satisfied and stoned BF. "Not even a blowjob, huh?" Jeff asked.

"I was really, REALLY horny" Cora winked.

"Babe what, what changed your mind?" Jeff asked.

"Don't worry about it" Cora said. "Let's just say I had a change of heart."

"Okay" Jeff didn't feel like now was a good time for intense questions. "Were you serious about being fucked in the butt, like, every day?" he asked hopeful.

"Maybe, depends if you're a good boy or not" Cora said, giving him a neck kiss or two.

"Hey, weren't...weren't you saying something about like, Maddie doing something? Like with you?"

Cora's head shot up. "Y-yeah. How does that sit with you?"

"Like, what was she gonna do, again?" Jeff asked.

"It was a joke" Cora tried to play it off. "She would train my ass to take your cock, which you said would be hot, remember?"

"Yeah it would, but like…Maddie wouldn't go for that."

"You'd be surprised" Cora muttered.

"What?"

"Nothing. Nothing at all. I love you Jeff. Like a lot, and thanks for being patient" Cora said, giving him a host of kisses.

"I love you too, babe. Hey, you wanna like, sleep over, or something? It's really late."

"I thought you'd never ask."

Jeff turned off the stereo and the lights and jumped back into bed with Cora. She rubbed his cock for a few minutes while he drifted off to sleep. Cora wanted to tell Jeff that Maddie fucked her, but…something in her gut wanted to keep it a secret. True, Jeff was really high and probably up for anything, but sober Jeff was a completely different guy, and she definitely didn't want to upset him…maybe he wouldn't care for his girlfriend's lesbian roommate taking her anal virginity? Obviously, this was a topic of conversation Cora had to keep under wraps, considering she now had two different stories to both Jeff and Maddie, figuring she would tell the truth in time…

Though as she drifted off to sleep, she hoped that would result in the two punishing her ass simultaneously. That was definitely something Cora could sink her teeth…or rather her ass into. She fell asleep, satisfied of the turn of events in her favor.

Back over to Maddie, she too was about to fall asleep in her own bed. Maddie knew what she had to do; she had to confront Cora. She was a bit salty of letting her horny side get the better of her and would definitely not fuck her anymore. She remained steadfast in her convictions…or did she?

As Maddie laid there, desperately trying to be the good Christian girl, her hand moved to her pussy, and she remained awake, masturbating to Cora bending over to have her ass fucked again. Maddie sighed. This wasn't going to be easy, but after all, it was her who recommended this tushy technique in the first place.

Oh well, this was a conundrum to be sure, but at least it couldn't get any worse. Maddie gave up on trying to orgasm and slowly drifted off to sleep in the hot room of her hot apartment, ready for the dawn of a new day.

**Notes for the Chapter:**

> Thanks for reading, do leave a comment with your suggestions for future chapters!

**Author's Note:**

> Do leave a comment with your suggestions. They may appear in later chapters.


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